本研究使用不同的觸媒進行酚之溴化反應，藉以瞭解這些觸媒的功能。酚的溴化反應中使用 KBr 做為溴源、H2O2 做為氧化劑、醋酸做為溶劑，反應時間分別為 0.5、1、2、4 小時，反應溫度分別為室溫、低溫（15℃）。
對酚的溴化反應主要分為三組：（1）使用層狀磷酸鈦(HTP)固體酸，（2）使用酸性陽離子交換樹脂（Amberlyst-15），（3）無添加觸媒。利用氣相層析儀（GC）對三組反應產物做定量分析，可得知三組之間的反應結果差異，並進行探討。
無觸媒的反應結果顯示反應產物以4-溴酚為主，對照使用陽離子樹脂或層狀磷酸鈦的反應結果，可觀察到對4-溴酚產物的選擇性較好，對2-溴酚產物的選擇性較差。
使用層狀磷酸鈦為觸媒在酚的溴化反應中，反應時間2小時、反應溫度為室溫的條件下可得到3組反應中最高的轉化率92%。推測可能是層狀磷酸鈦的表面積較陽離子交換樹脂大，因此可與更多的反應物接觸進行催化反應，或是由於層狀磷酸鈦表面分佈較多的布忍斯特酸進行催化而獲得較高轉化率。
本研究亦對層狀磷酸鈦(HTP)固體酸進行表面積與孔徑分析，其平均表面積為9.15 m2/g，平均吸附孔徑為1.57μm。

Bromination of phenol was studied by using different kinds of catalysts. Potassium bromide was employed as the source of bromine, hydrogen peroxide as oxidant, acetic acid as solvent. The reactions were carried out at different temperatures and various reaction times.
The reactions were also categorized into three groups: (1) using layered titanium phosphate (HTP) solid acid as catalyst, (2) using proton type cationic exchange resin Amberlyst-15 as catalyst, (3) using no catalyst. Gas chromatography was employed for the analysis of the reaction results.
It was found that the reaction using HTP as catalyst with reaction time of 2 hours at room temperature gave the highest yield of 92%. It is possibly due to the larger surface area, which is 9.15 m2/g obtained from BET experiment, of the HTP powder with comparison to that of Amberlyst-15.

明志科技大學碩士學位論文指導教授推薦書 I
明志科技大學碩士學位論文口試委員審定書 II
明志科技大學學位論文授權書 III
誌謝 IV
明志科技大學 IV
摘要 V
Abstract VI
圖目錄 IX
表目錄 XI
表目錄 XI
第一章 緒論 1
1.1 前言 1
1.2 研究動機 2
第二章 相關理論與文獻回顧 4
2.1 相關原理 4
2.1.1水熱合成法 4
2.1.2 X光繞射分析儀 5
2.1.3 親電性芳香取代反應原理 7
2.1.4取代基的配位效應 10
2.1.5氣相層析儀(Gas chromatography) 10
2.2 文獻回顧 11
2.2.1 酚的特性 11
2.2.2 酚主要產物的應用 12
2.2.3 酚的反應 14
2.2.4 酚的溴化反應 17
2.2.5 觸媒的特性 23
2.2.6固體酸觸媒 24
2.2.7陽離子交換樹脂 26
2.2.8磷酸鈦觸媒 27
第三章 實驗內容 29
3.1 實驗藥品與器材 29
3.1.1 實驗藥品 29
3.1.2 實驗器材 31
3.2 實驗步驟 32
3.2.1 合成層狀磷酸鈦(HTP)觸媒 33
3.2.2以XRD鑑定觸媒 33
3.2.3 酚的溴化反應 34
3.2.4 製做檢量線 36
3.2.5 產物的GC定量分析配製 40
第四章 結果與討論 41
4.1層狀磷酸鈦（HTP）觸媒做XRD的鑑定 41
4.2層狀磷酸鈦（HTP）觸媒FE-SEM掃描分析 43
4.3層狀磷酸鈦（HTP）的表面積與孔徑分析結果 45
4.4將產物做GC-MS定性分析 46
4.5 標準品檢量線與層析圖 50
4.6 將產物做GC定量分析 59
4.7酚的溴化反應討論 69
4.7.1酚的溴化反應 69
4.7.2各組反應在溴化反應中的轉化率結果比較 70
4.7.3改變反應溫度對各組反應轉化率的影響 73
4.7.4反應產物選擇率以及反應產物受熱力、動力控制的比較 76
第五章 結論 83

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